144001-01-4Relevant academic research and scientific papers
Efficient synthesis of a complete donor/acceptor bis(aryl)diyne family
Holmes, Brian T.,Pennington, William T.,Hanks, Timothy W.
, p. 2447 - 2461 (2003)
A facile route to a family of bis(aryl)diynes containing both an electron donating pyridine ring and an electron accepting iodobenzene has been developed. The convergent synthesis involves the coupling of 2-, 3-, or 4-bromopyridine with TMS-acetylene, followed by deprotection to form the first half of the molecule. Similarly, 2-, 3-, or 4-iodoaniline was coupled to TMS-acetylene after protection of the amine group as a diethyltriazine. After conversion of the triazine to an iodine, deprotection of the acetylene and formation of the corresponding bromophenyl-acetylene, the two halves of the molecule were coupled under Cadiot-Chodkiewicz conditions. Nine new compounds were prepared, each of which was found to thermally polymerize from the melt. None of the compounds underwent photochemical polymerization in the solid-state.
Sulfoximine version of double elimination protocol for synthesis of chiral acetylenic cyclophanes
Orita, Akihiro,De, Lie An,Nakano, Takehiko,Yaruva, Jayamma,Ma, Nianchun,Otera, Junzo
, p. 2005 - 2010 (2007/10/03)
A new strategy for constructing enantiopure acetylenic cyclophanes is described on the basis of one-pot double elimination reaction starting from dialdehydes and bis(sulfoximine)s. In this case, the conventional sulfone protocol affords poorer yields of t
